


Stiles and Jackson

by distraughtlover



Series: Stiles, You Lucky Bastard [5]
Category: Teen Wolf (TV)
Genre: Bottom Jackson Whittemore, M/M, Plot What Plot/Porn Without Plot, Top Stiles Stilinski
Language: English
Status: Completed
Published: 2018-02-18
Updated: 2018-02-18
Packaged: 2019-03-20 20:52:02
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,812
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13725744
Author URL: https://archiveofourown.org/users/distraughtlover/pseuds/distraughtlover
Summary: Stiles goes to Jacksons house to pick something up, and ends up spending the night instead.





	Stiles and Jackson

The last semester had started to flow quickly along.

Before Stiles realized, it was the middle of February. The Spring semester always seemed to go faster than the fall, and before, he had been fine with that, but now that most people were waiting on college acceptance letters or celebrating what certain college they had already been accepted to, it made the quickness of this semester feel frightening. 

Stiles and Scott had applied to the same University in town (University of Beacon Hills, or UBH, was a fantastic college, especially since their city had almost a million citizens) and even though the prospect of leaving and going to another college like Berkeley or somewhere else excited Stiles, he also kept UBH as a backup just in case he didn't get in somewhere else, or if he simply wanted to stay home. 

He wasn't completely worried about the future. It hadn't even arrived yet, so there was no point in dwelling on what could possibly happen.

It was the end of the school week, and the lacrosse team did not have a game, which meant Stiles had the entire weekend to relax. The past few weeks had been quiet regarding him being naked in bed with another naked man. After him and Scott had fucked a month ago, they both decided it would be the best if it remained a one-time thing. Stiles had been feeling that way for a bit, and he was relieved when Scott brought it up.

They both knew that nothing had changed between them, it was just that continual sex between good friends most of the time did not end well. It was funny, because both of them felt guilty for wanting to stop any more sex between them, and they realized that their friendship was still just as strong, if not even more. 

And besides, they both looked fondly at their time in the sack together, and twenty years down the line when they were still best friends, it wouldn't even be a big deal. 

But luckily for Stiles, there were still three other guys who wanted to do the dirty with him whenever the chance happened. He was still in love with the fact that these gorgeous, muscular hunks wanted to bottom for him every time, although he thought it would only be fair that at some point they would have to top him. 

It would happen eventually. But hey, as long they kept wanting his dick in their asses, Stiles wouldn't complain. He had been doing quite the opposite of complaining. 

So far, Stiles and Danny had only had sex the one time, but they both had not been able to get around to each other for a hot rendezvous because of schedules and what not. Although they had both communicated that it would need to happen soon.

As for Derek, Stiles had fucked him a couple more times, each one somehow being better than the last. He still got extremely hot thinking about how enthusiastic Derek was to have his dick in his mouth (and hole). 

And Isaac, they had only had sex one more time since their first. 

But what a night it was.

All in all, Stiles was having the absolute best time, and he was going to thoroughly enjoy it for as long as he could. 

He was now home, school being done for the day and the whole weekend looming ahead. His dad was done with work for the day, and they had just enjoyed what felt like one of their first meals together in a while. 

It was seven when Stiles got a text from Jackson, saying that he had forgotten his notebook in class and Jackson had it, asking if he wanted to pick it up. Stiles didn't even realize he had left it behind, until remembering that he was in a hurry to get to his next class and must have forgot it. 

He didn't exactly feel like driving just to get one item, but figured it wouldn't hurt. 

"Hey dad, you mind if I stop at Jacksons real quick? I forgot a notebook from school and he has it for me," Stiles said to his dad.

"That's fine, son. Just be careful. Are you gonna spend the night or anything?" Sheriff Stilinski asked.

Stiles laughed and said, "Nah, Jackson and I aren't that close."

The sheriff laughed as well and said, "Yeah, I know. But once you're out and about, you never know."

"Well, I'll ask you if I change my mind or something," Stiles said.

After grabbing his wallet and keys, Stiles said goodbye to his dad and hopped in his jeep, started it up, and drove off in the direction of Jacksons house. 

If this had happened at the beginning of freshman year, Stiles would have been weirded out. But, considering that him and Jackson were actually on friendly terms, it didn't seem so odd. 

When he arrived at his house, Stiles parked in front and got out, walking to the front door and ringing the doorbell. Jackson opened the door and greeted Stiles with a cool smile.

"Hey Stiles. Come on in," Jackson said.

Stiles walked in and him and Jackson gave each other a casual guy handshake, but he was in awe of Jacksons house. It was a two-story house with high ceilings and noticeable crown molding. To his left from the front door was an enclosed study and to his right was a formal dining room. 

They walked further into the house and entered the large living room situated around a warm fireplace with a mounted TV above. The updated kitchen sat behind in an open-concept. 

"Hey, so thanks for letting me know about my notebook," Stiles said to Jackson.

"Yeah, no problem," Jackson said, pointing to his notebook that lay on the nearby kitchen counter. "You want something to drink?"

"No thanks, I'm good. I don't really want to waste anymore of your time, so I'll just head out," Stiles said.

"Don't worry, you're not wasting my time. You can hang for a bit if you want," Jackson said, sitting down on the sofa in the living room.

Stiles suddenly felt like he would be rude if he immediately left after just arriving, so he sat next to Jackson on the sofa and watched the program that Jackson had left playing on the TV. 

"So, are your parents chilling in their room?" Stiles asked.

"Nah, they're out of town for the weekend, but they'll be back on Sunday, so I have the house to myself," Jackson said.

"That's sweet. No parties or anything?" Stiles joked.

Jackson laughed and said, "No, not this time. Besides, I was kind of hoping," Jackson said, sliding inconspicuously closer to Stiles, "that you and I could have our own party."

Stiles gave him a confused look and asked, "What do you mean?"

Jackson smirked and said, "What would you say to you and I having a little bit of…fun?"

Jackson's hand began slowly rubbing Stiles' thigh with just the slightest touch. He was shocked that Jackson was making a move on him, especially to have sex, and he questioned him.

"Uh, are you seriously asking me to have sex with you?" Stiles asked, his surprise evident.

Jackson wasn't deterred and said, "I was trying to be subtle and sexy, but yeah, I am."

"Wow, um," Stiles said, trying to find the right words, and continued, "I'm not opposed or anything, but I didn't think you found me attractive. At all. Are you sure you're not just lonely tonight?"

"Stiles, you're hot. Like, seriously hot. Plus, you've grown into yourself and I've definitely noticed. And I know we weren't on the best terms freshman year, but I'd say we're at a pretty good point now," Jackson said.

"Damn. Well, I seriously appreciate that, but I'm still sure you could find a better guy than me," Stiles said.

He didn't know where this feeling of negativity came from. Maybe it was because he felt uncomfortable around Jackson, who was literally the prettiest twink ever, and perhaps he was feeling unworthy next to him. 

"Nope, my mind has been set on you. Now, if you're not interested in me, then just let me know and I'll stop so I don't embarrass myself anymore," Jackson said laughing.

"I'm definitely interested," Stiles said with a smile.

"Good," Jackson said, then leaned forward and kissed Stiles, who scooted closer to him. 

Stiles' lips danced with Jackson's, their connection eliciting a wonderful feeling within. Jacksons hands held onto Stiles' shoulders firmly while Stiles' hands traveled and stayed at Jackson's sides. 

When things were starting to heat up, Jackson pulled away.

"Let's take this upstairs," Jackson said.

Stiles could only muster a nod, his mind going hazy with lust. As they stood up and walked, Stiles noticed that he was the slightest bit taller than Jackson, and also slightly thicker, which surprised him. Ever since Jackson had left the lacrosse team, he had focused more on being thin and muscular, rather than buff and large for sports. In Stiles' opinion, it looked great on Jackson. 

Then, once they neared Jackson's bedroom upstairs, he started to worry. With the other men that Stiles had been with, they were all tops who had asked him to fuck them. But with Jackson, it was becoming clearer that he was a true bottom, and Stiles felt nervous about being a good top. 

They entered Jacksons large bedroom and Stiles took note of it. Once entered, to the left was a king-sized bed that faced outward. A small couch was placed on the right, and on the left side of the bed was an open door that presumably led to an en-suite bathroom. 

Stiles quickly texted his dad that he would be hanging for a bit, and then Jackson latched himself onto Stiles. He groaned as Jackson kissed his neck fervently and hands traveled underneath his shirt.

"Damn, Stiles. Let's get this shirt off," Jackson said.

Without dwelling on his nerves, Stiles grabbed the bottom of his shirt and pulled it over his head, dropping it to the carpeted floor. Jackson smiled at the sight and Stiles felt less worried.

"Wow. You've definitely grown up," Jackson purred, his index finger drawing down Stiles' chest.

"Yup, I'm all grown up. Everywhere," Stiles said with a slight grin.

Jackson smirked, and then slowly pulled off his own shirt, revealing the toned, smooth, flat, defined chest underneath. Without warning, Jackson went back to Stiles' lips and they went at it, both of their hands taking off each-others pants. When they were just left in their underwear, they climbed onto Jacksons bed, then shimmied out the last of their clothes. 

As Stiles lay naked in bed with an equally naked Jackson, he realized that it would never get old being naked with another guy. Being gay just kept getting better and better. 

They hungrily made out, and Jacksons delicious moans drove Stiles harder, making him groan from the pleasure he felt. He was laying on top, and he began grinding against Jackson, whose hands went down and held Stiles' butt. Their hard cocks rubbed together and created an almost unbearable heat. 

Then, Jacksons hand went to Stiles' chest, rubbing for a few seconds before pushing him onto his back. Stiles propped himself up and watched as Jackson went down to his dick, then began jerking him off. 

Stiles groaned heavily as he watched Jacksons clenched hand jerk his cock at a furious pace, slow down for a bit, and then resumed at a quick, ferocious pace. It was incredibly hot to see Jackson this way. 

Without warning, Jacksons hot mouth descended on Stiles' stiff cock, lips wrapping around his length. He went slow at first, dragging his mouth up and down while Stiles arched upwards, in disbelief at the hot center around his dick. Jackson popped his mouth off, held his length, and slapped it down repeatedly on his tongue, aching for the taste of Stiles' cock.

Stiles scooted up so his back rested against the headboard, and Jackson continued working his cock. Letting go, Jackson began sucking Stiles' dick without any hands, with a quick, eager pace to match. His hot breath ghosting over his length, Jackson lapped at the underside until he reached the head and sucked it by itself.

"Oh my god, don't fucking stop," Stiles groaned.

Jackson's energy was at a great level which fueled how well he sucked Stiles' penis. Still with no hands, his mouth reached all the down, engulfing the length entirely with his warm mouth. 

Then, his mouth went down to Stiles' hanging balls, giving each of them love and attention. 

"Fuck, your balls smell so good," Jackson moaned. 

Licking each one thoroughly, he then sucked them with vigor and swirled both around in his mouth, eventually pushing them out with a loud pop. 

Stiles decided it was time to give Jackson his due attention and so he grabbed him by the shoulders and hoisted him up, depositing him on his back so he could go to work.

Grabbing Jacksons thick, nice-sized length, Stiles went down and lapped repeatedly, getting acquainted before sucking him fully. His mouth worked up and down while Jackson moaned from above. With one hand resting on Jacksons thigh, Stiles held his cock with the other and jerked him off while sucking simultaneously. After getting his fill of Jackson's balls, he rubbed his hands up and down Jacksons thighs.

"Let me eat that ass," Stiles said.

"Hold on," Jackson said.

Jackson moved forward from his position, and, in what seemed like no time at all, he lifted his entire lower half, bringing his legs all the way back to his face, so now he was just laying on basically his neck, with his perfect ass up in the air.

"Holy fuck, that's the hottest thing I've seen," Stiles said, getting up and standing on his knees. 

Even harder than he was already, Stiles held Jackson's ass, caressing the smooth firm skin before descending on his gorgeous hole. His tongue reached out and he took his time, gently licking the top of his entrance at a slow pace. Jackson was a moaning mess underneath as Stiles circled his rim over and over. Wanting to make sure Jackson was prepared first, Stiles then worked up a storm.

Like the horndog he was internally, Stiles began devouring Jackson's hole, his tongue doing the ABC's at a hungry pace. Gripping his cheeks, Stiles ate him out like there was no tomorrow, internally hoping there was though.

"Oh fuck, spank my ass," Jackson said.

Stiles happily obliged and slapped his hand against Jacksons ass, in love with the perfect bubble butt he held in his hands. After doing that a couple more times, Stiles went back to his hole, pushing his tongue inside and just about bursting from the pleasure.

"Get your fingers in me," Jackson just about demanded.

Stiles sucked his own index finger and dragged it across Jacksons hole, eventually pushing in. Both groaned and Stiles pushed his finger in and out, getting hot from the tightness surrounding his digit.

Wanting to work at a quicker pace, Stiles pulled his finger out, sucked two of them to get them slick, and pushed both of them in. Jackson moaned and begged for more, so Stiles fingered him as quick as he could. 

Slipping his fingers out, Stiles then patted Jacksons hole with the flat of his hand a few times, then slipped his middle finger in and pushed down. Needing more of the taste, Stiles went back and licked his entrance furiously.

"Yeah, eat that fucking ass," Jackson said.

After pushing his tongue inside as much as he could, Stiles decided that he needed to fuck Jackson before he exploded. 

Jackson dropped his legs and turned over to his bedside table, pulling out the top drawer and bringing forth a packaged condom and a bottle of lube. He gently tossed the condom to Stiles and put the lube by his side.

Grabbing the condom, Stiles opened it up and rolled it down his hard cock, then coated it with lube while Jackson got on all fours in front of him. 

Scooting forward on his knees, Stiles reached out and held Jacksons side, then asked, "Ready?"

Jackson nodded encouragingly and Stiles positioned his covered cock in front of Jacksons hole, gently pushing the head of his dick in. He held his length as it slowly went further inside Jackson, eventually letting go once he was all the way in. Both of them groaned in pleasure and Stiles' grip on Jacksons side intensified.

He slowly backed his cock out then slid all the way back in, repeating the pleasurable action a few more times before Jackson said, "I'm good, fuck me." 

Stiles quickened his speed and began groaning from having his dick sliding in and out of Jacksons perfect ass, the tightness and wonderful heat becoming greater by the second. 

His hands moved down and held the sides of Jacksons butt while he snapped his hips forward and back, groaning while Jackson urged him on. 

"Oh, yeah! Come on, fuck me hard!" Jackson yelled. 

Jackson reached his hand back and caressed Stiles' muscular side as he continued to rock his dick inside him. He was in love with how good it felt to have his hole filled up by Stiles' fantastic cock and he wanted even more.

Stiles already felt himself working up a sweat from fucking Jackson, which only made him want to go even harder. As he slammed inside Jackson, the sound of their skin slapping together mixing with their heavy breaths created a sensual score within Jacksons bedroom. 

When Stiles slowed down his rhythm, they knew it was time for another position. He slipped his cock out of Jackson who turned around and hungrily kissed Stiles. They made out naked standing on their knees before Jackson pushed him around so he was laying on his back, resting against the pillows. 

Then Jackson climbed into his lap and grabbed his stiff cock, holding it in place before sinking his ass down on it. Stiles' cock slid in without an issue and the immediate tightness had Stiles moaning loudly. 

Jackson gently began to move, rocking forward and back on Stiles' dick, moaning at being completely filled by a nice thick cock. Stiles' hands went and held onto his sides, eventually going down and gripping Jackson's perfectly round tight butt. Jackson increased his speed and grinned lustily down at Stiles, caressing his chest. Stiles' mouth was open wide from the amount of pleasure he was getting as Jackson continued to fuck his cock. 

"Put your arms back," Jackson said.

Stiles did so, moving his arms and resting them behind his head, then smiled widely as Jackson bounced up and down, thoroughly enjoying the show. 

"Ride that fucking cock," Stiles said.

Jackson moaned out continuous 'ohs' and 'ahs' which hardened Stiles' cock even more. When his bouncing began to slow, Stiles pushed up his hips repeatedly and Jackson moaned heavily in pleasure. He resumed bouncing his butt and Stiles praised him.

With his arms still resting behind his head, Stiles said, "Come on, keep fucking my cock."

Somehow, Jackson went even faster and Stiles felt like he was blasting off to paradise, moving his arms and holding on to Jacksons ass. He was so freaking glad he came over and that this was how he was spending his Friday night.

Jackson rose up and let Stiles' dick fall out of his ass. They both moved and Jackson got on his back while Stiles went in front of him.

Grabbing Jacksons thigh, Stiles then pushed his dick forward inside Jackson and resumed fucking him.

Stiles was in awe at the ecstasy he felt from being inside another mega-hot guy's ass and he wondered if Jackson was going to want to continue this.

As he pounded Jackson, he latched onto his own cock and jerked it off.

"Oh fuck, I'm gonna cum," Jackson said.

Stiles fucked him harder while Jackson jerked off, and then he came with a moan as his cum splattered in strips across his chest. 

It wouldn't be long now before Stiles came, and he felt his imminent release on its way. 

"Shit, I'm about to burst," Stiles said. 

"Do it on my face," Jackson said.

Stiles pounded him as hard as he could, groaning from all the pleasure he felt.

When he felt ready, Stiles pulled out and took the condom off. Jackson quickly got up and went on the floor on his knees while Stiles stood up and quickly jerked his cock.

"Shoot that manly cum all over my face," Jackson said.

"Oh fuck, I'm gonna-" Stiles said before groaning loudly as he ejaculated. 

Each pump sent Stiles over the edge. He felt out of himself from how much pleasure this was. Stiles watched as each strip of white cum splashed Jacksons face. One long strip landed from his forehead down to his nose, and part of another strip hit Jacksons hair. One other coated his cheek while the last two landed on Jacksons eyes. 

They both were breathing heavily. Stiles' chest heaved and he watched as Jackson looked up at him, his face covered in cum and still full of lust. 

Jacksons tongue darted out and licked at the cum near his lips, then he swiped a finger across his cheek and ate the cum he collected.

"Mmmm, your cum tastes delicious," Jackson moaned.

He ate a couple more swipes and then stood up, pushing Stiles back onto the bed.

Stiles lay facing the bathroom and Jackson walked towards it, his gorgeous ass only for Stiles' eyes. Then he stopped, his back still facing Stiles. He turned his head, looked at Stiles, and said, "By the way, you're spending the night."

He closed the bathroom door. 

Stiles was panting as he lay naked on Jacksons bed. He smiled, and then it turned into a full on grin. His cock had started to soften, but then it hardened again after picturing Jacksons face covered in his cum. 

Realizing what Jackson said, Stiles stood up and walked to his pants where his phone was, grabbing it and sending a text to his dad asking if he could spend the night. A response came a couple minutes later, saying that it was alright since it was Friday. 

He hopped back into the bed, and then Jackson came out, his face and chest clear. He walked towards him and got into bed, both of them laying nude next to each other.

"My dad said I could spend the night," Stiles said. 

"Good, cause we're not through yet," Jackson said. 

They took a good restful nap, and then went at it two more times throughout the night.


End file.
